Although the temperatures can reach -40 degrees (so cold that it is the same in both Celsius and Fahrenheit!), Chicago is still definitely worth a visit in the winter. The museums are terrific, hotels are more reasonably priced, and there is so much to do!
What to do
The Art Institute of Chicago is an absolute must, with impressive works by Van Gogh, Warhol, Picasso, and many others, including lots of impressionist painters. You can spend two full days there. (Try the salmon salad in The Café. Get there when it opens (11 a.m.) to avoid the crowds.)
Other great museums include the Museum of Science and Industry and the Shedd Aquarium. The Peggy Notebaert Nature Museum and the Lincoln Park Zoo are both good options for a winter day.
Chicago has stunning architecture! (My favorite is the Wrigley Building along Michigan Avenue.) Take the Riverwalk or even an architectural tour.
Explore the shops on Broadway, including Cram at 3331 N. Broadway
Where to stay
I always stay at the Hotel Versey, now part of Hilton’s Tapestry Collection. Located at 644 West Diversey Parkway, just south of the “gayborhood,” it is full of shops and restaurants. The rates are lower during the week (and during the winter). You also get free use of the LA Fitness next door (with an indoor pool). Parking is available. Trader Joe’s and Barnes and Noble are across the street, and the Fresh Market is steps away.
Nightlife
Just up the street from the Hotel Versey is the gayborhood formerly known as Boystown (now known as Northalsted).
Make your first stop at the iconic video megabar, Sidetrack (3349 N. Halsted). I like the show tunes, which run multiple days, including 4 p.m. on Sunday.
You will find go-gos and dancing at Hydrate (3458 N. Halsted). Sunday Funday features $4 wells.
Also fun is the Kit Kat Club (3524 N. Halsted).
The leather bar Cell Block (3702 N. Halsted) is very cruisy.
The Lucky Horseshoe (3169 N. Halsted) has dancers.
The Center on Halsted is the community center. A Whole Foods and senior housing is in the complex as well.
For bar ads and maps, pick up a copy of Grab, Chicago’s monthly LGBTQ+ publication or read it online at www.GRABChicago.com. It is full of local happenings.
Where and what to eat
Stan’s Donuts (at the corner of Clark and Diversey) has terrific donuts, breakfast burritos, and more.
The new Lucky Cat coffee bar (2806 N. Clark) is just around the corner from the Hotel Versey and has better coffee than both Starbucks and Stan’s (which are also nearby).
I like the shrimp salad at Trader Joe’s (667 W. Diversey).
Rosati’s (953 W. Diversey, just east of the Diversey CTA station) has megaslices of pizza for just $6.
The Fresh Market (2730 N. Halsted at Diversey) has hot food, a nice croissant breakfast sandwich, and even wine.
Tuk Tuk Thai Isan Street Food (2852 N. Clark, next to Century Plaza), my current favorite, features great curry and Thai dishes (including a jug of water to go with the spicy red curry).
Getting there
I took the Amtrak from Milwaukee. There are six round trips a day, with only three stops, and it goes 90 mph. From Detroit, Indianapolis, St. Louis, DC, and even Seattle and SF, you can also take Amtrak to Chicago.
I flew United out of O’Hare back to Indy — a great airline, with new equipment, enjoyable entertainment, and professional staff, as well as being located in a beautiful terminal. Take the Blue Line CTA to O’Hare via the Diversey bus to Logan Square CTA.
For more information
Grab Chicago Magazine (online and in print) for a good map of the bar scene areas. You can pick up a copy at Sidetrack and other locations.
Winter is a perfect time to visit Chicago: The crowds are gone. The hotel rates are reasonable. And you can see how the locals enjoy this top-rate American city.
Bill Malcolm, North America’s only LGBTQ travel columnist, has written over a hundred columns over the last 10 years, which have run in LGBTQ publications, the IGLTA.org website, and other forums. He focuses on value and going local. And he boycotts hotels with resort fees, destination fees, amenity fees, and other junk charges. He pays his own way and received no compensation of any kind for this column.
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